Cyclohexene → 2-Amino-4-(4-methylpiperazin-1-yl) benzoic acid tertbutyl ester

HRID 1487394Notes

Reaction equation

C1CCCCC=1.[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:16]([N+:27]([O-])=O)[CH:15]=2)[CH2:10][CH2:9]1>[Pd].C(O)C>[NH2:27][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][N:8]([CH3:7])[CH2:9][CH2:10]2)[CH:26]=[CH:25][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

0.160 g (1.500 mmol) of palladium on carbon (10%) and 15.19 ml (150 mmol) of cyclohexene are added to a solution of 4.82 g (15 mmol) of tert-butyl 4-(4-methylpiperazin-1-yl)-2-nitrobenzoate in 100 ml of ethanol. The reaction mixture is heated at a temperature of 80° C. for 8 hours. The reaction mixture is filtered and then rinsed with ethanol to yield 4.2 g (yield=96%) of tert-butyl 2-amino-4-(4-methylpiperazin-1-yl)benzoate in the form of a yellow solid.

Workup

filtrationThe reaction mixture is filtered
washrinsed with ethanol

Sources & evidence

ORD record: ord-8ccfd343ba0945c9b4cd376a3660e17f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428510B2

Reaction notes

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